Alkali-amide controlled selective synthesis of 7-azaindole and 7-azaindoline through domino reactions of 2-fluoro-3-methylpyridine and aldehydes
Alkali-amide controlled selective synthesis of 7-azaindole and 7-azaindoline through domino reactions of 2-fluoro-3-methylpyridine and aldehydes
复制标题
通过2-氟-3-甲基吡啶和醛的多米诺反应，碱酰胺控制选择性合成7-氮杂吲哚和7-氮杂吲哚啉
DOI：
10.1039/d2qo00339b
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发表时间：
2022
影响因子：
5.4
通讯作者：
Mao, Jianyou
中科院分区：
文献类型：
--
作者：
Xu, Xinyu;Ou, Mingjie;Wang, Yan-En;Lin, Tingzhi;Xiong, Dan;Xue, Fei;Walsh, Patrick J.;Mao, Jianyou
氮杂吲哚和氮杂吲哚啉是药物和天然产物的重要核心结构，在药物化学领域有着广泛的应用。在这项研究中，我们开发了一种新的一锅法选择性地合成7-氮杂吲哚和7-氮杂吲哚啉，它可以通过容易获得的2-氟-3-甲基吡啶和芳基醛之间的反应生成。LiN（SiMe 3）2生成7-氮杂吲哚，KN（SiMe 3）2生成7-氮杂吲哚，其化学选择性依赖于电荷。在这些条件下可以引入一系列取代基，为进一步的加工和官能化提供手柄。
Azaindoles and azaindolines are important core structures in pharmaceuticals and natural products, which have found wide applications in the field of medicinal chemistry. In this study, we developed a novel one-pot method for selectively synthesizing 7-azaindoles and 7-azaindolines, which can be generated by reactions between the readily available 2-fluoro-3-methylpyridine and arylaldehydes. The chemoselectivity is counterion dependent, with LiN(SiMe3)2 generating 7-azaindolines and KN(SiMe3)2 furnishing 7-azaindoles. A range of substituents can be introduced under these conditions, providing handles for further elaboration and functionalization.